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Issue 12, 2009
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Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules

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Abstract

The selective recognition of substrates or cofactors is a key feature of biological processes. It involves coordination bonds, hydrogen bonding, charge/charge and charge/dipole interactions. In this Perspective, we describe how the calix[6]arene core can be functionalized and shaped to act as a biomimetic molecular receptor. The strategy relies on the selective introduction of three amino arms on alternate phenolic positions. Upon metal ion binding or self-assemblyvia multiple ion-pairing and H-bonding, these amino arms are projected towards each other, thus closing the calixarene small rim. The resulting cone-shaped receptors act as molecular funnels displaying high affinities for a variety of neutral guests. Their hosting properties can be finely tuned by changing the small or the large rim or by allosteric effects. Induced-fit processes are also often observed as the cavity can expand for large guests or shrink for small ones. Hence, the different families of calix[6]arene-based receptors presented here highlight the importance of having a flexible and polarized hydrophobic structure to accommodate the guest.

Graphical abstract: Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules

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Publication details

The article was received on 06 Feb 2009 and first published on 23 Apr 2009


Article type: Perspective
DOI: 10.1039/B902456E
Citation: Org. Biomol. Chem., 2009,7, 2485-2500
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    Biomimetic and self-assembled calix[6]arene-based receptors for neutral molecules

    D. Coquière, S. Le Gac, U. Darbost, O. Sénèque, I. Jabin and O. Reinaud, Org. Biomol. Chem., 2009, 7, 2485
    DOI: 10.1039/B902456E

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